


Never

by basil_leaf



Category: Supernatural
Genre: Angst and Fluff and Smut, Blow Jobs, F/M, Light Angst, Lingerie, Reader-Insert, Smut, Teasing, Vaginal Sex
Language: English
Status: Completed
Published: 2016-12-23
Updated: 2016-12-23
Packaged: 2018-09-11 07:36:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,936
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8969644
Author URL: https://archiveofourown.org/users/basil_leaf/pseuds/basil_leaf
Summary: After a hunt, you witnesses Dean trying to pick up a girl in a bar.  You’re not having it though and, in your frustration, you scare the girl off.  Dean is not happy about that but, after a conversation with the hunter, you make it up to him.





	

“And you’ve really never, you know, done it before?” the girl asked, tossing her long, bleached blonde hair over her shoulder.

“I guess I just haven’t found the right girl,” Dean murmured as he ran a finger up her tanned arm, eliciting a giggle from the girl. 

You snorted at that but it went unnoticed by the amorous pair. You were at the bar with the Winchesters after a long hunt. Initially when you had started hunting with the brothers, the three of you would share one motel room but after one too many bathroom mishaps, cock blocks, and hurting backs from someone inevitably sleeping on a tiny couch or the floor, you’d all decided to spring for two rooms when you were on the road. The way you divided the rooms was simple: the first person to take someone “home” from the bar got the single room. Dean won the race the most often, but you and Sam each pulled with enough frequency that he would occasionally muse about renting a third room.

Tonight, however, you were more than happy to share the room tonight with whichever brother was too slow to pick up a lady. You had volunteered as bait for the hunt and ended up pretty battered before the Winchesters had been able to get to you. The only reason you were even at the bar was because Sam had used most of the whiskey to sterilize your cuts and the needle he’d used to stitch you up, leaving nothing for you to drink.

You sat and listened as Dean continued to run his game on the unsuspecting girl. She was still giggling and the sound had you rolling your eyes.

“I just, I can’t believe it,” she cooed at him, clearly taken in by his story. “Never?”

“Never,” Dean replied sincerely. 

Knowing the hunter as well as you did, you could see the lie written across his face but someone with less experience reading Dean would miss it for sure. You let out a full on sarcastic laugh and the girl turned toward you. 

“Excuse me, but do you have some kind of problem?” she asked. “I think it’s sweet.”

“And I bet you’re hoping he’s found the right girl tonight, honey,” you replied, your voice dripping with sweetness. “Can you seriously look at this man and honestly believe he’s never had sex? He’s a modern day Adonis. I’ve lost count of the number of women I’ve heard him bang through the thin walls of a motel room.”

The woman turned her glare toward Dean. “Is that true?” she asked.

“Hey, at least you know you’ll be in for a good time,” Dean tried, giving her his most charming smile but the girl just rolled her eyes and walked away.

“What the hell, Y/N?” Dean asked, his frustration clear in his voice. “You’re miserable so the rest of us can’t have a good night? You gonna go cockblock Sam next?”

As if his name summoned him, Sam appeared behind Dean wearing his jacket. “I’ll see you guys in the morning,” he told you both with a grin, completely oblivious to the tone of the conversation he was interrupting. You watched and Dean glared as Sam sauntered to the door, taking a red haired woman by the hand and leading her out of the bar. 

“God damnit,” he muttered before turning back to you. “I don’t care if you have to sleep in the car, I am getting laid tonight.” Dean began to scan the room for another girl but you grabbed his face and made him look at you. 

“Screw you, Winchester,” you spat at him. “In case you didn’t notice, I played bait and almost got killed today, Dean. I lost a lot of blood and there’s no way in hell I’m sleeping in the damn car. If hooking up is that important to you, you can take the car. I’m going back and going to bed.” You tossed a few bills onto the bar, more than enough to cover your drinks, and hopped off of your stool before shrugging on your jacket. As you made your way toward the door, you played up the little limp you had from a twisted knee. It wasn’t even a hunt related injury - you’d slipped on some ice just after the brothers had rescued you - but Dean didn’t need to know that.

You could feel his eyes on you during your entire walk to the door. The motel wasn’t far, probably about a fifteen minute walk, so you were surprised when he caught up to you as you walked past the Impala. 

“Now that it looks like I’ve chased away two girls, no one in there is going to give me the time of day,” Dean explained. “I may as well head back, too.”

“I’m sure there’s some loose woman with even looser morals in there,” you replied, still walking. 

“Don’t be an idiot, get in the car.” You could hear the impatience in Dean’s voice. 

You huffed, your breath leaving your mouth in a puff of steam. It was rather cold out and the trip would take less than half the time if you rode with Dean. Your mind made up, you climbed into the Impala, riding up front in what was usually Sam’s seat.

“Look, I’m sorry for that misery loves company line in there,” Dean apologized. “You’ve had a hell of a day and Sam and I probably should have been more focused on making sure you were alright rather than on getting laid.” Dean wasn’t one to make apologies all that often and, though he was staring straight ahead at the road with an unreadable face, his voice was sincere.

“It’s alright. I’m sorry I chased that girl off,” you offered in reply. “I shouldn’t have done that. But you shouldn’t have been lying to her like that, either.”

“You’d be surprised how many girls fall for that line,” Dean smirked. 

“Seriously? And they still believe they were your first even when you’re done?” you asked him incredulously.

“Wow, you’re such a fast learner,” Dean responded, raising his voice in imitation of a woman’s and making you laugh. “That was the best sex I’ve ever had, I can’t believe you were a virgin!”

“The best sex they’ve ever had, huh?” you laughed, quirking an eyebrow at the older Winchester. “Someone sounds a little full of himself.”

“Seven out of ten women tell me that, and I’m sure the other three are thinking it,” Dean shared as he wagged his eyebrows at you, his voice dropping back to it’s normal octave. “I could show you if you’d like.”

“Screw you, Winchester,” you said for the second time that night but this time the words were mixed with laughter, holding none of the venom from earlier. You playfully swatted his arm, making sure to not hit him so hard it would have an effect on his driving as he pulled into the hotel parking lot and parked the Impala outside of the room you two were sharing. Dean turned to look at you, considering his next words carefully. Seeming to come to a decision, he spoke: “Well, if you insist. I did tell you I’d be getting laid tonight.”

You rolled your eyes at his joke as he got out of the car and jogged around to your door, arriving just as you stood from the seat. He grabbed you around your waist and threw you over his shoulder, holding you in a fireman’s carry as he slammed the car door shut and walked walked toward your motel room.

“Put me down!” you hissed, kicking your legs and pounding your fists half heartedly against his back. Even though you were pretty sure Dean wouldn’t drop you, you didn’t want to squirm too much. Your injuries were extensive enough that you didn’t need to add a 6 foot fall to the list on the off chance that you did manage to wiggle out of his grasp.

“Not a chance,” Dean answered and you could hear the grin in his voice. “Like you said back there, you’re hurt. And don’t think I didn’t notice that limp in the bar. I’m gonna take good care of you tonight, Princess.” 

Princess, that was a new nickname. You pondered it for a moment and almost missed it when he murmured “Should have been taking care of you from the start.” You didn’t know what he meant by that, but he sounded so sincere when he said it. He was speaking quietly enough that you were certain that he hadn’t meant for you to hear the words so you decided not to ask him about them for now.

When he made it inside the motel room, he deposited you on one of the beds and made his way to your duffle bag. “Dean, what are you…” but you were cut off when he pulled something out of the bag, a victorious look on his face. He was holding the pajamas you saved for the nights when you won the private motel room, a lace and satin chemise. The piece was your favorite color and made you feel sexy and powerful whenever you wore it. 

Dean tossed the chemise onto the bed along with a pair of sweatpants and a t-shirt. “I’m going to take a quick shower. Why don’t you put on some pajamas and we’ll see where the night takes us.”

He was giving you the choice, you realized. He wanted you but wasn’t sure if you returned that sentiment. He had already showered before the two of you and Sam had gone to the bar and now he was giving you the time and space to think this over and make a decision. If you put on the sweats, he’d climb into his own bed and the two of you would probably pick a movie to watch as you fell asleep. But if you put on the lingerie… 

You couldn’t deny that you had a crush on the older Winchester. Hell, you’d have to be blind not to and, even then, his voice alone would probably have done it for you anyway. If you were being honest with yourself, part of what had made you so irritable at the bar was jealousy fueled by being in such close proximity to Dean’s pickup attempt. But you didn’t want to be just another notch in his belt. Nothing could make a friendship awkward more quickly than a one night stand. You had to talk to Dean first.

Dean emerged from the bathroom in nothing but a pair of boxer briefs, clearly surprised to see you still sitting on the bed in the clothes you had worn to the bar. 

“Dean, what do you want from this? From us?” you questioned, trying to keep your tone light but serious. The last thing you wanted was to sound accusatory. 

The question caught Dean off guard and he stuttered a bit before forcing out a reply. “I want whatever you’re willing to give me. Friendship, one night,” he paused before almost whispering, “more…” Dean cleared his throat and sat down on the bed next to you, laying all his cards on the table “Look, I know you think of Sam and I as brothers but you and me, I think we could be so much more.”

“Then, why all the random women?” you asked, truly curious but expecting him to deflect the question. You knew just as well as anyone that Dean never talked about his feelings if he could avoid it. 

But the hunter surprised you by answering your question. “Trying to fuck you out of my system, I guess,” Dean was speaking so quietly and sounded so tired. “You always made it so clear that you see us as siblings so if I couldn’t have you, the closest woman would suffice.”

“That was my coping mechanism,” you confessed, “the brother thing. I figured that maybe if I said it enough, I’d start to believe it.”

Dean looked at you with hope in his eyes for the first time since he’d come out of the shower. “What do you mean?”

“I think you forgot to brush your teeth, Dean,” you told him. “Why don’t you go take care of that and we can finish talking when you’re done.”

He looked confused again but got up and returned to the bathroom to finish up his nightly routine. When he came back into the main room his face lit up as he crossed over to where you were laying on the bed, draped in satin and lace.

He drank you in with his eyes before sitting on the edge of the bed. “That really is a great color for you, Y/N,” Dean remarked, his voice husky as he ran a hand up your thigh and then over the fabric that covered your hip. His hand continued its journey over your ribs and shoulder before finally coming to rest, cupping your cheek as he leaned in and pressed a kiss to your lips.

Dean pulled away and you couldn’t resist getting in one last sarcastic jab. You put on your best valley girl voice and asked, “So, like, you’ve really never, like, done, you know, this before?” 

Dean leaned in to kiss you again and you could feel the smile on his lips. “Never like this.”

You hummed into the kiss, and the two of you continued making out for a little while, Dean’s tongue requesting entry into your mouth. You opened up to him and sucked on his tongue, giving the man a preview of what was to come. Releasing his tongue, you lightly bit down on his lower lip, eliciting a moan from the man beside you. 

You pulled away from his mouth and pushed against his shoulder. Dean got the hint and rolled to lie on his back. You sat up and threw one of your legs over him, straddling his groin as you settled in on top of him. Dean’s hands flew to your hips and pulled you down as he ground into your satin covered core. You moaned at the contact. It was simultaneously perfect and not enough. 

You leaned down and began kissing Dean again, not lingering too long in any one place. Your lips moved from his mouth to his ear, giving him a little nip, then down the column of his neck, which you noted was particularly sensitive. You’d have to keep that in mind for later. You continued kissing your way down his body, pausing to give each of his nipples some attention and again to dip your tongue into his belly button. When you got to the elastic of Dean’s underwear, you ran your tongue from one hip bone to the other before taking the waistband between your teeth and dragging his boxer briefs down his legs.

“Holy hell, Y/N,” Dean groaned as he watched you through hooded eyes. The hunter began squirming as you slowly licked and kissed your way back up his legs, gently biting his inner thigh. “Y/N…” he gasped at one bite that was a little less gentle. 

Finally, after teasing him for a just a little longer, you moved to where Dean so badly wanted you. But instead of taking him in your mouth, you licked your palm and wrapped your hand around his erection, giving him a few slow pumps. You looked up at Dean’s face and could only think of one word to describe him in this state: beautiful. His head was thrown back against the pillows, his green eyes shut tightly, and his mouth was open, silently asking for more.

If he wanted more, you would be happy to give it to him but only on your time. You continued to slowly stroke his erection with your saliva slicked hand as you took the head of his cock into your mouth. Dean groaned with pleasure at the attention of your mouth and tongue. You focused on the tip until Dean was squirming beneath you once again, his hands bunching in the sheets as he tried to stop himself from tangling his fingers in your hair to urge you on. 

“Oh God,” he breathed, unable to form more words than that. “Oh… oh… oh God, more. Need more.”

You smiled around the tip of Dean’s cock at his inability to form a sentence and, after one last hard suck, you moved your hand and took his entire length into your mouth.

“Holy fuck,” Dean panted as you hollowed your cheeks and began to bob your head, the sensations nearly overwhelming him after the concentrated effort on his head. His hands finally flew from the sheet and landed on your head, not pushing or pulling, per se, but his fingers knotted in your hair, tugging on the strands and making you moan around him. The vibrations shot through his body and his back and hips arched off of the bed, burying his cock even deeper in your throat. You swallowed around him, humming at the taste of him (and, if you were being honest, just to drive him a little more wild). His hands grabbed a firmer hold in your hair and this time, his fingers were pulling at your head, moving your mouth off of him.

“I’m gonna… Don’t wanna… not in your mouth. I need to be inside of you…” Dean’s voice was wrecked and his pupils were blown wide, you could barely make out the green of his eyes. You crawled up the hunter’s body and caught his lips in a kiss. He moaned at the taste of himself on your tongue. You continued kissing for a few more moments before you slid off of the bed.

“Where are you…” Dean started but you distracted him. As you bent over your duffle bag, you kept your knees straight, causing the hem of your lingerie to ride up over you ass and exposing your dripping, satin covered pussy. You wiggled your ass at him, knowing full well there was a dark, wet patch showing through the material that was hiding you from his vision. 

You found what you wanted rather quickly but extended your search for a few more seconds, enjoying the power you held over the hunter. Eventually, you stood up straight and sashayed back towards Dean, holding the corner of the condom wrapper between your teeth. You were about to open the wrapper when Dean stopped you. 

“As sexy as you look, you’re still wearing way too many clothes, Princess,” he told you, some of his mental faculties returning after your assault on his cock had ended, apparently. He stood from the bed and walked toward you. He took the condom from your mouth and placed it on the night stand before taking you in his arms and kissing you again. As he kissed you, his hands worked their way under your chemise, tracing lines and shapes on your back, your sides, and your stomach. He lifted the garment up, breaking the kiss long enough to pull it over your head before diving back down to your mouth. 

Dean played with the ties that held your panties up, running his fingers up and down your hips before he pulled on the strings, releasing the fabric from your body and letting it fall to the ground. With both of you now naked, Dean backed up until his knees were against the bed and sat down, his mouth moving to your breasts and stomach. He continued to kiss your body, making you writhe and moan before he finally pulled back entirely and took in your nude form. 

“Beautiful,” you heard him whisper. 

Dean shifted so he was lying back on the pillows again and cocked an eyebrow in your direction. “Now, where were we?” he asked with a smirk, his voice full of charm and snark.

You grabbed the condom from the nightstand and ripped open the wrapper before rolling the latex down his length and giving him a few more pumps and a squeeze for good measure. You considered teasing him more but you were aching with desire for this man so, instead, you straddled his hips and reached between your legs to line up his cock with your entrance. You slowly lowered yourself down onto his length, your breath catching in your throat as you felt him stretch you, opening you up in the best possible way. Once you were fully seated, you chanced looking at Dean’s face. The man was the epitome of pure sex. His lower lip was caught between his teeth and, as if he could feel your gaze on him, his eyes flew open and locked with yours. 

You experimentally rolled your hips a few times and, once you were used to having his cock buried inside of you, you began moving in earnest. Dean’s hips thrusted up to meet yours with every stroke of his cock in your silky, wet folds. Soon, the room was a cacophony of pants, moans, and groans, neither of you capable of much more than speaking the other’s name and the occasional hiss of “yes” or “more.” You threw your head back as you rode Dean, a look of pure ecstasy on your face. Dean’s hands went to your hips and after one particularly deep thrust, he held you in place, using his strength to flip you both, his cock never leaving the warm heat of your body. Now on top of you, Dean took one of your legs and placed it over his shoulder. In this new position, he was able to drive even deeper into you, his hardness gliding over your sweet spot with every thrust. 

“Oh, god… Dean… Dean… Dean…” you chanted his name, “I’m so close.” You could feel the heat that had been pooling in your belly spreading; you were on the precipice of your orgasm, about to tumble over. 

One of Dean’s hands moved from your hip to where your bodies were joined. He rubbed circles into your clit, causing you to cry out in pleasure. As your orgasm hit you, you bit down on the juncture where Dean’s neck met his shoulder. The combination of your walls squeezing his cock and the pain/pleasure sensation created by your teeth scraping over his skin sent him over the edge, too, and he groaned your name as his release hit him. 

Dean collapsed on top of you and you both lay there, spent and breathing hard for a few moments. You continued to lave attention on Dean’s neck, grateful that you hadn’t drawn blood but dead set on leaving a bruise, marking your man. 

All too soon, Dean was gingerly pulling out of you and rolling off of the bed. He made his way to the bathroom and when he returned, he had a warm washcloth. Dean carefully, lovingly cleaned you up, telling you more with his actions than he’d be able to share with his words. After cleaning himself up, too, he returned the cloth to the bathroom and came back to bed, cuddling in beside you. He took you in his arms and placed a sweet, gentle kiss on your temple. 

Just as you were about to drift off to sleep, you heard a creaking sound followed by muffled moans from the room next door. You broke into a fit of giggles, which, in turn, made Dean laugh as well. “Maybe we should give Sam his own room more often,” you mused.

**Author's Note:**

> The first half of this story is also posted on my tumblr, revwinchester.tumblr.com (it stops right before the smut on tumblr). Hope you enjoyed it! <3


End file.
